4,4'-(2,3-Dimethyltetramethylen)dibrenzcatechin

Nordihydroguaretic acid

HCID 4534CAS 500-38-9
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Grundinformationen

Standard-SMILES
CC(Cc1ccc(O)c(O)c1)C(C)Cc1ccc(O)c(O)c1
InChIKey
HCZKYJDFEPMADG-UHFFFAOYSA-N
Summenformel
C18H22O4
Durchschnittliche Molmasse
302,4 g/mol
Monoisotopische Masse
302,15180918

Überblick

Nordihydroguaiaretic acid is a tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor. It has a role as a ferroptosis inhibitor, a geroprotector, an antioxidant and a plant metabolite. It is a lignan, a member of catechols and a tetrol.

Namen und Bezeichner

Bevorzugter Name
Nordihydroguaretic acid
IUPAC
4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
Lokaler Name
4,4'-(2,3-Dimethyltetramethylen)dibrenzcatechin
Englischer Name
Nordihydroguaiaretic acid
Summenformel
C18H22O4
Molmasse
302.36

Namen und Synonyme

nordihydroguaretic acid2,3-bis(3,4-dihydroxybenzyl)butaneRefChem:854717NORDIHYDROGUAIARETIC ACID500-38-9NDGA4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diolNorhydroguaiaretic acidNorguaiaretic acid, dihydro-1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-NSC 42914,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
Weitere Namen anzeigen
ACTINEXNORDIHYDROGUAIRETIC ACIDTIMTEC-BB SBB005930LABOTEST-BB LT00233087NDGA, LARREA DIVARICATAnordihydroguaiareticacidihydronorguaiareticaciddihydro-norguaiareticaci
MFCD000022062,3-Bis(3,4-dihydroxyphenylmethyl)butaneDTXSID5022437Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)nordihydroguaiaretateCHEMBL52Butane, 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-

Datenbank-Bezeichner

CAS
500-38-9
PubChem CID
4534
DTXSID
DTXSID5022437
ChEMBL
CHEMBL52
ChEBI
CHEBI:7625
EC Number
207-903-0
Nikkaji
J9.195B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,3
Polarare Oberfläche (TPSA)
80,9 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
5
Schwere Atome
22

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Plant Toxins
CosmeticsAntioxidant
Food AdditivesANTIOXIDANT -> FDA Substance added to food
Endocrine DisruptorsPotential endocrine disrupting compound
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionSolid; [Merck Index] White odorless powder; [Alfa Aesar MSDS]

Physikochemische Eigenschaften

Schmelzpunkt
184 · 184-186 °C (lit.)
Siedepunkt
363.4 °C · 363.4°C (rough estimate)
Dichte
1.0772 · 1.0772 (rough estimate)
Brechungsindex
1.423 · 1.4230 (estimate)
storage temp.
Inert atmosphere,Room Temperature
Löslichkeit
DMSO (Slightly), Methanol (Slightly)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 188 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationChemical: 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
Hazards SummaryThis CAS# refers to the unspecified stereoisomer form; The meso- form is CAS# 27686-84-6; [Merck Index] A skin and strong eye irritant; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

wgk
3
hs_code
29072990
RTECS-Nr.
UX1750000
risk_code
22-36/37/38
hazard_code
Xn
safety_code
26-36/37-37/39-24/25-22

Chemie und Industrie

Verwendung und Herstellung

Uses · 2 Einträge

Occurs in the creosote bush; Used as an antioxidant in foods and as an antineoplastic; [Merck Index]

Banned for use as an antioxidant in food; [EPA]

Use Classification · 3 Einträge

Food Additives -> ANTIOXIDANT -> JECFA Functional Classes

Food Additives -> ANTIOXIDANT -> JECFA Functional Classes

Cosmetics -> Antioxidant

Anwendungen · 1 Eintrag

BeschreibungNordihydroguaiaretic acid (NDGA) is a grayish-white crystalline compound that was widely used as an antioxidant in animal fats in the 1950s and 1960s. It possesses phenolic properties similar to gallates, including their advantages and disadvantages. Besides the isolation of natural material (resinous exudate of creosote bush), NDGA has also been chemically synthesized. As the result of unfavorable toxicological findings, NDGA is prohibited from use in the US. More specifically, NDGA is a potent lipoxygenase inhibitor which interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carbox- ylesterase,and,to a lesser extent, cyclooxygenase.

Darstellung · 1 Eintrag

synthetischeNordihydroguaiaretic acid is obtained by hydrodemethylation of dimethyl ether of guaiacolinic acid, a component of guaiac resin. It is also produced from desert plant, creosote bush (Larrea divaricata Cav. Or Corillea tridentate), which can be widely found in the border zone of southern of USA and northern of Mexico.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Anbieter50 Anbieter

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
成都健腾生物技术有限公司028-85159085 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Nordihydroguaiaretic acid is a tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor. It has a role as an antioxidant, a plant metabolite, a ferroptosis inhibitor and a geroprotector. It is a member of catechols, a tetrol and a lignan.

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